Hydroxyamine hydrochloride → HCID 66631721, compound

HRID 405024Notes

Reaction equation

C([O:3][C:4](=[O:35])[CH:5]([NH:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:22][CH:21]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[NH:16])[NH:14][OH:15])=[C:9]([F:17])[CH:8]=1)C.C(OC(=O)C(N[C:52](=O)[C:53]1[CH:58]=[CH:57][C:56]([NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[CH:55][CH:54]=1)CC1C=CC(C#N)=C(F)C=1)C.NO.Cl.C([O-])(O)=O.[Na+]>CCO>[C:30]([O:29][C:27]([NH:26][C:23]1[CH:22]=[CH:21][C:20]([C:19]([NH:18][CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:16]=[C:52]([C:53]4[CH:54]=[CH:55][C:56]([NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[CH:57][CH:58]=4)[O:15][N:14]=3)=[C:9]([F:17])[CH:8]=2)[C:4]([OH:3])=[O:35])=[O:34])=[CH:25][CH:24]=1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 120 °C

Procedure

2-(4-tert-Butoxycarbonylamino-benzoylamino)-3-[3-fluoro-4-(N-hydroxycarbamimidoyl)-phenyl]-propionic acid ethyl ester. A mixture of 2-(4-tert-butoxycarbonylamino-benzoylamino)-3-(4-cyano-3-fluoro-phenyl)-propionic acid ethyl ester (214 mg, 0.47 mmol), NH2OH.HCl (49 mg 0.71 mmol), and NaHCO3 (79 mg, 0.94 mmol) in EtOH (10 mL) was heated under microwave at 120° C. for 20 min and then allowed to cool to room temperature. The mixture was filtered, concentrated in vacuo, and purified by silica gel chromatography to give the title compound (170 mg) as a white solid.

Workup

temperatureto cool to room temperature
filtrationThe mixture was filtered
concentrationconcentrated in vacuo
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-b88088ae3b2f4ce9b31a09f11bdb35b9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748412B2

Reaction notes

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